Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells

Jacquot, Yves; Laı̈os, Ioanna; Cleeren, Anny; Nonclercq, Denis; Bermont, Laurent; Refouvelet, Bernard; Boubekeur, Kamal; Xicluna, Alain; Leclercq, Guy; Laurent, Guy

doi:10.1016/j.bmc.2007.01.025

Cited by 38 publications

(21 citation statements)

References 34 publications

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“…Excitation wavelength of 560 nm and emission wavelength of 590 nm were used for the observation of Texas Red fluorescence. Image acquisition and analysis were performed as described in a previous publication (Jacquot et al 2007). Median fluorescence intensities were computed from the analysis of w80-120 nuclei in each control or treated culture.…”

Section: Western Blot Analysismentioning

confidence: 99%

Effect of nuclear export inhibition on estrogen receptor regulation in breast cancer cells

Nonclercq

Journé²,

Laı̈os³

et al. 2007

Journal of Molecular Endocrinology

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We used the Crm1 inhibitor leptomycin B (LMB) to examine a possible involvement of nuclear export in estrogen receptor a (ER) level and function in MCF-7 breast carcinoma cells. As revealed by immunofluorescence microscopy and western blotting with anti-ER antibodies, LMB produced an accumulation of ER in cell nuclei. LMB also partly abrogated ER elimination resulting from Hsp90 disruption and 17b-estradiol (E 2 )-induced ER downregulation. By contrast, it was ineffective on ER downregulation caused by the pure anti-estrogen fulvestrant. Finally, LMB inhibited E 2 -induced progesterone receptor expression and the expression of an estrogen response element-driven luciferase reporter gene in unstimulated and E 2 -stimulated cells. Altogether, the data reported here suggest that: i) ER undergoes nuclear export directly or indirectly involving exportin Crm1; ii) degradation of unliganded and of agonist-bound ER probably occurs in an extranuclear compartment, while it is not the case for ER bound to a pure anti-estrogen; and iii) optimal ER-mediated gene transactivation seems to require nucleocytoplasmic shuttle of the receptor.

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Section: Western Blot Analysismentioning

confidence: 99%

Effect of nuclear export inhibition on estrogen receptor regulation in breast cancer cells

Nonclercq

Journé²,

Laı̈os³

et al. 2007

Journal of Molecular Endocrinology

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“…1 H NMR spectra were recorded on Bruker 300 MHz spectrometer. 13 was added to a microwave tube equipped with a magnetic stir bar. The microwave tube was fitted with a reflux condenser and irradiated in a microwave reactor at a temperature of 130 C for 3 min Fig.…”

Section: Methodsmentioning

confidence: 99%

“…Coumarin Mannich bases [12] inhibited carraggeenin-induced hind paw edema and found to possess protective properties against adjuvant-induced arthritis in rats. 4-Amino-3-(2-methylbenzyl)coumarin derivatives [13] exhibited potent estrogenic activity on the estrogen receptor positive (ER þ ) human MCF-7 breast cancer cell line. 4-Hydroxy coumarin derivatives [14] showed pronounced prolongation of prothrombin time with anticoagulant values similar to that of warfarin.…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

Puttaraju

Shivashankar

Chandra

et al. 2013

European Journal of Medicinal Chemistry

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Microwave assisted synthesis of dihydrobenzo [4,5]imidazo [1,2-a] pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo [4,5] In general, all the compounds possessed better antifungal properties than antibacterial properties. The coumarin substituted dihydrobenzo [4,5]imidazo[1,2-a]pyrimidin-4-one (4g) (R ¼ i-Pr, R 1 ¼ 6-Cl) was found to be the most potent cytotoxic compound (88%) against Dalton's Ascitic Lymphoma cell line at the concentration of 100 mg/mL.

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“…ERα data were normalized according to actin (ERα / actin) and expressed in percent of control (untreated cells). Ability of bisphenol (# 23) to antagonize E 2 -induced downregulation of ERα was further assessed by immunofluorescence microscopy using an experimental protocol described previously [26].…”

Section: Page 11 Of 44mentioning

confidence: 99%

Capacity of type I and II ligands to confer to estrogen receptor alpha an appropriate conformation for the recruitment of coactivators containing a LxxLL motif—Relationship with the regulation of receptor level and ERE-dependent transcription in MCF-7 cells

Bourgoin-Voillard¹,

Gallo²,

Laı̈os³

et al. 2010

Biochemical Pharmacology

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Capacity of type I and II ligands to confer to estrogen receptor alpha an appropriate conformation for the recruitment of coactivators containing a LxxLL motif -Relationship with the regulation of receptor level and ERE-dependent transcription in MCF-7 cells. Biochemical Pharmacology, Elsevier, 2009, 79 (5) This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.Page 1 of 44 A c c e p t e d M a n u s c r i p *Graphical AbstractPage 2 of 44 A c c e p t e d M a n u s c r i p t

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Synthesis, structure, and estrogenic activity of 4-amino-3-(2-methylbenzyl)coumarins on human breast carcinoma cells

Cited by 38 publications

References 34 publications

Effect of nuclear export inhibition on estrogen receptor regulation in breast cancer cells

Effect of nuclear export inhibition on estrogen receptor regulation in breast cancer cells

Microwave assisted synthesis of dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones; synthesis, in vitro antimicrobial and anticancer activities of novel coumarin substituted dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-4-ones

Capacity of type I and II ligands to confer to estrogen receptor alpha an appropriate conformation for the recruitment of coactivators containing a LxxLL motif—Relationship with the regulation of receptor level and ERE-dependent transcription in MCF-7 cells

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